1040916-66-2Relevant academic research and scientific papers
The cycloacylation - 1,3-acylrearrangement sequence as tool for highly substituted pyrrolones
Buehrdel, Gunther,Beckert, Rainer,Friedrich, Birgit,Goerls, Helmar
, p. 845 - 851 (2008)
(Chemical Equation Presented) The cyclization reactions between bis-imidoylchlorides 1 and ketones, which possess different CH-acidity, were investigated. Diphenylacetone 2 reacts under mild conditions via C,O-cyclization of the preformed enolate to yield the iminofurane derivative 3. Upon treatment with trifluoroacetic acid, the latter can be rearranged quantitatively into the pyrrolone 5. In contrast, 1,3-acetonedicarboxylate 9 and cyclohexanone 12 immediately lead to highly substituted pyrrolones 11 and 14. Obviously, the primarily formed cyclization products undergo a very fast 1,3-acyl rearrangement (Dimroth-/Mumm-Rearrangement). The structures of the maleiimide 11 and the indolone 14 were determined by single crystal X-ray structure analysis. Due to its amino/imino substructure, compound 3 is an efficient ligand for metal complexation reactions, exemplified by the synthesis of two different Zn-complexes 7 and 8.
